9-Deoxy-9-methylene-PGF-type lactones

ABSTRACT

This invention comprises certain analogs PGE or 11-deoxy-PGE compounds in which the carbonyl at C-9 is replaced by methylene. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 682,848,filed May 4, 1976, now issued as U.S. Pat. No. 4,060,534 on Nov. 29,1977; which is a continuation-in-part of Ser. No. 651,622 filed Jan. 23,1976, issued as U.S. Pat. No. 4,021,467 on May 3, 1977; which is adivision of Ser. No. 556,768, filed Mar. 10, 1975, issued as U.S. Pat.No. 3,950,363 on Apr. 13, 1976.

The present invention relates to prostaglandin analogs, for which theessential material constituting disclosure therefor is incorporated byreference here from Ser. No. 682,848.

I claim:
 1. A prostaglandin of the formula ##STR1## wherein Y₁ istrans--CH═CH--, --C.tbd.C--, or --CH₂ CH₂ --, wherein R₇ is --(CH₂)_(m)--CH₃, wherein m is one to 5, inclusive, or ##STR2## WHEREIN Z₃ is oxaor methylene and s is zero, one, 2, or 3 and T is chloro, fluoro,trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy ofone to three carbon atoms, inclusive, with the proviso that not morethan two T's are other than alkyl, the various T's being the same ordifferent, and the further proviso that Z₃ is oxa only when R₃ and R₄are hydrogen or methyl, being the same or different;Wherein R₅ ishydrogen or methyl; Wherein L₁ is ##STR3## wherein R₃ and R₄ arehydrogen, methyl, or fluoro, being the same or different, with theproviso that one of R₃ and R₄ is fluoro only when the other is hydrogenor fluoro, and wherein Z₇ is (1) cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --,(2) cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --, (3) cis--CH₂--CH═CH--(CH₂)_(g) --CH₂ --, (4) --(ch₂)₃ --(ch₂)_(g) --CH₂ --, (5)--(ch₂)₃ --(ch₂)_(g) --CF₂ --, (6) --ch₂ --o--ch₂ --(ch₂)_(g) --CH₂ --,(7) --c.tbd.c--ch₂ --(ch₂)_(g) --CH₂ --, (8) --ch₂ --c.tbd.c--(ch₂)_(g)--CH₂ --, ##STR4## wherein g is one, 2, or
 3. 2. A prostaglandin analogaccording to claim 1, wherein Y₁ is --CH₂ CH₂ --.
 3. A prostaglandinanalog according to claim 2, wherein Z₇ is cis--CH═CH--CH₂ --(CH₂)_(g)--CF₂ --.
 4. 9-Deoxy-9-methylene-2,2-difluoro-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 3. 5. Aprostaglandin analog according to claim 2, wherein Z₇ is --(CH₂)₃--(CH₂)_(g) --CF₂ --. 6.9-Deoxy-9-methylene-2,2-difluoro-13,14-dihydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 5. 7. A prostaglandin analogaccording to claim 2, wherein Z₇ is cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂--.
 8. 9-Deoxy-9-methylene-cis-4,5-didehydro-13,14-dihydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 7. 9. Aprostaglandin analog according to claim 2, wherein Z₇ is --CH₂ --O--CH₂--(CH₂)_(g) --CH₂ --.
 10. 9-Deoxy-9-methylene-5-oxa-13,14-dihydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 9. 11. Aprostaglandin analog according to claim 2, wherein Z₇ is --C.tbd.C--CH₂--(CH₂)_(g) --CH₂ --. 12.9-Deoxy-9-methylene-5,6-didehydro-13,14-dihydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 11. 13. A prostaglandin analogaccording to claim 2, wherein Z₇ is --CH₂ --C═C--(CH₂)_(g) --CH₂ --. 14.9-Deoxy-9-methylene-4,4,5,5-tetradehydro-13,14-dihydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 13. 15. Aprostaglandin analog according to claim 2, wherein Z₇ is --(CH₂)₃--(CH₂)_(g) --CH₂ --.
 16. A prostaglandin analog according to claim 15,wherein R₅ is R₅.
 17. 9-Deoxy-9-methylene-15-epi-13,14-dihydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 16. 18. Aprostaglandin analog according to claim 15, wherein R₅ is --R₅.
 19. Aprostaglandin analog according to claim 18, wherein m is 3, s is zero orone, and T is chloro, fluoro, or trifluoromethyl.
 20. A prostaglandinanalog according to claim 19, wherein g is
 3. 21.9-Deoxy-9-methylene-2a,2b-dihomo-15-methyl-13,14-dihydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 20. 22.9-Deoxy-9-methylene-2a,2b-dihomo-13,14-dihydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 20. 23. A prostaglandin analogaccording to claim 19, wherein g is one.
 24. A prostaglandin analogaccording to claim 23, wherein at least one of R₃ and R₄ is methyl. 25.A prostaglandin analog according to claim 24, wherein R₃ and R₄ are bothmethyl.
 26. 9-Deoxy-9-methylene-16,16-dimethyl-13,14-dihydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 25. 27. Aprostaglandin analog according to claim 23, wherein at least one of R₃and R₄ is fluoro.
 28. A prostaglandin analog according to claim 27,wherein R₃ and R₄ are both fluoro. 29.9-Deoxy-9-methylene-16,16-difluoro-13,14-dihydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 28. 30. A prostaglandin analogaccording to claim 23, wherein R₃ and R₄ are both hydrogen.
 31. Aprostaglandin analog according to claim 30, wherein R₅ is methyl. 32.9-Deoxy-9-methylene-15-methyl-13,14-dihydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 31. 33. A prostaglandin analogaccording to claim 30, wherein R₅ is hydrogen. 34.9-Deoxy-9-methylene-13,14-dihydro-PGF₁, 1,15-lactone, a prostaglandinanalog according to claim
 33. 35. A prostaglandin analog according toclaim 2, wherein Z₇ is cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --.
 36. Aprostaglandin analog according to claim 35, wherein R₅ is R₅.
 37. Aprostaglandin analog according to claim 36, wherein m is 3, s is zero orone, and T is chloro, fluoro, or trifluoromethyl.
 38. A prostaglandinanalog according to claim 37, wherein g is
 3. 39.9-Deoxy-9-methylene-2a,2b-dihomo-15-epi-15-methyl-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 38. 40.9-Deoxy-9-methylene-2a,2b-dihomo-15-epi-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 38. 41. Aprostaglandin analog according to claim 37, wherein g is one.
 42. Aprostaglandin analog according to claim 41, wherein at least one of R₃and R₄ is methyl. 43.9-Deoxy-9-methylene-15-epi-16,16-dimethyl-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 42. 44. Aprostaglandin analog according to claim 41, wherein at least one of R₃and R₄ is fluoro. 45.9-Deoxy-9-methylene-15-epi-16,16-difluoro-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 44. 46. Aprostaglandin analog according to claim 41, wherein R₃ and R₄ are bothhydrogen.
 47. 9-Deoxy-9-methylene-15-epi-15-methyl-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 46. 48. Aprostaglandin analog according to claim 35, wherein R₅ is R₅.
 49. Aprostaglandin analog according to claim 48, wherein m is 3, s is zero orone, and T is chloro, fluoro, or trifluoromethyl.
 50. A prostaglandinanalog according to claim 49, wherein g is
 3. 51. A prostaglandin analogaccording to claim 50, wherein at least one of R₃ and R₄ is methyl. 52.9-Deoxy-9-methylene-2a,2b-dihomo-16,16-dimethyl-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 51. 53. Aprostaglandin analog according to claim 50, wherein at least one of R₃is fluoro. 54.9-Deoxy-9-methylene-2a,2b-dihomo-16,16-difluoro-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 53. 55. Aprostaglandin analog according to claim 50, wherein R₃ and R₄ are bothhydrogen. 56.9-Deoxy-9-methylene-2a,2b-dihomo-15-methyl-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 55. 57. Aprostaglandin analog according to claim 49, wherein g is one.
 58. Aprostaglandin analog according to claim 57, wherein at least one of R₃and R₄ is methyl.
 59. A prostaglandin analog according to claim 58,wherein R₃ and R₄ are both methyl. 60.9-Deoxy-9-methylene-16,16-dimethyl-13,14-dihydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 59. 61. A prostaglandin analogaccording to claim 57, wherein at least one of R₃ and R₄ is fluoro. 62.A prostaglandin analog according to claim 61, wherein R₃ and R₄ are bothfluoro.
 63. A prostaglandin analog according to claim 62, wherein R₅ ismethyl. 64.9-Deoxy-9-methylene-15-methyl-16,16-difluoro-13,14-dihydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 63. 65. Aprostaglandin analog according to claim 62, wherein R₅ is hydrogen. 66.9-Deoxy-9-methylene-16,16-difluoro-13,14-dihydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 65. 67. A prostaglandin analogaccording to claim 57, wherein R₃ and R₄ are both hydrogen.
 68. Aprostaglandin analog according to claim 67, wherein R₅ is methyl. 69.9-Deoxy-9-methylene-15-methyl-13,14-dihydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 68. 70. A prostaglandin analogaccording to claim 67, wherein R₅ is hydrogen. 71.9-Deoxy-9-methylene-13,14-dihydro-PGF₂, 1,15-lactone, a prostaglandinanalog according to claim
 70. 72. A prostaglandin analog according toclaim 1, wherein Y₁ is --C.tbd.C--.
 73. A prostaglandin analog accordingto claim 72, wherein Z₇ is cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --. 74.9-Deoxy-9-methylene-2,2-difluoro-13,14-didehydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 73. 75. A prostaglandin analogaccording to claim 72, wherein Z₇ is --(CH₂)₃ --(CH₂)_(g) --CF₂ --. 76.9-Deoxy-9-methylene-2,2-difluoro-13,14-didehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 75. 77. A prostaglandin analogaccording to claim 72, wherein Z₇ is cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂--.
 78. 9-Deoxy-9-methylene-cis-4,5-didehydro-13,14-didehydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 77. 79. Aprostaglandin analog according to claim 72, wherein Z₇ is --CH₂ --O--CH₂---(CH₂)_(g) --CH₂ --. 80.9-Deoxy-9-methylene-5-oxa-13,14-didehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 79. 81. A prostaglandin analogaccording to claim 72, wherein Z₇ is --C.tbd.C--CH₂ --(CH₂)_(g) --CH₂--.
 82. 9-Deoxy-9-methylene-5,6,13,14-tetradehydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 81. 83. A prostaglandin analogaccording to claim 72, wherein Z₇ is --CH₂ --C.tbd.C--(CH₂)_(g) --CH₂--.
 84. 9-Deoxy-9-methylene-4,4,5,5,13,14-hexadehydro-PGF₁,1,15-lactone, a prostaglandin according to claim
 83. 85. A prostaglandinanalog according to claim 72, wherein Z₇ is --(CH₂)₃ --(CH₂)_(g) --CH₂--.
 86. A prostaglandin analog according to claim 85, wherein R₅ is R₅.87. 9-Deoxy-9-methylene-15-epi-13,14-didehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 86. 88. A prostaglandin analogaccording to claim 85, wherein R₅ is R₅.
 89. A prostaglandin analogaccording to claim 88, wherein m is 3, s is zero or one, and T ischloro, fluoro, or trifluoromethyl.
 90. A prostaglandin analog accordingto claim 89, wherein g is
 3. 91.9-Deoxy-9-methylene-2a,2b-dihomo-15-methyl-13,14-didehydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 90. 92.9-Deoxy-9-methylene-2a,2b-dihomo-13,14-didehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 90. 93. A prostaglandin analogaccording to claim 89, wherein g is one.
 94. A prostaglandin analogaccording to claim 93, wherein at least one of R₃ and R₄ is methyl. 95.A prostaglandin analog according to claim 94, wherein R₃ and R₄ are bothmethyl.
 96. 9-Deoxy-9-methylene-16,16-dimethyl-13,14-didehydro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 95. 97. Aprostaglandin analog according to claim 93, wherein at least one of R₃and R₄ is fluoro.
 98. A prostaglandin analog according to claim 97,wherein R₃ and R₄ are both fluoro. 99.9-Deoxy-9-methylene-16,16-difluoro-13,14-didehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 98. 100. A prostaglandin analogaccording to claim 93, wherein R₃ and R₄ are both hydrogen.
 101. Aprostaglandin analog according to claim 100, wherein R₅ is methyl. 102.9-Deoxy-9-methylene-15-methyl-13,14-didehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 101. 103. A prostaglandin analogaccording to claim 100, wherein R₅ is hydrogen. 104.9-Deoxy-9-methylene-13,14-didehydro-PGF₁, 1,15-lactone, a prostaglandinanalog according to claim
 103. 105. A prostaglandin analog according toclaim 72, wherein Z₇ is cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --.
 106. Aprostaglandin analog according to claim 105, wherein R₅ is R₅.
 107. Aprostaglandin analog according to claim 106, wherein m is 3, s is zeroor one, and T is chloro, fluoro, or trifluoromethyl.
 108. Aprostaglandin analog according to claim 107, wherein g is
 3. 109.9-Deoxy-9-methylene-2a,2b-dihomo-15-epi-15-methyl-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 108. 110.9-Deoxy-9-methylene-2a,2b-dihomo-15-epi-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 108. 111. Aprostaglandin analog according to claim 107, wherein g is one.
 112. Aprostaglandin analog according to claim 111, wherein at least one of R₃and R₄ is methyl. 113.9-Deoxy-9-methylene-15-epi-16,16-dimethyl-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 112. 114. Aprostaglandin analog according to claim 111, wherein at least one of R₃and R₄ is fluoro. 115.9-Deoxy-9-methylene-15-epi-16,16-difluoro-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 114. 116. Aprostaglandin analog according to claim 111, wherein R₃ and R₄ are bothhydrogen. 117.9-Deoxy-9-methylene-15-epi-15-methyl-13,14-didehydro-PGF₂, 1,15-lactone,a prostaglandin analog according to claim
 116. 118. A prostaglandinanalog according to claim 105, wherein R₅ is R₅.
 119. A prostaglandinanalog according to claim 118, wherein m is 3, s is zero or one, and Tis chloro, fluoro, or trifluoromethyl.
 120. A prostaglandin analogaccording to claim 119, wherein g is
 3. 121. A prostaglandin analogaccording to claim 120, wherein at least one of R₃ and R₄ is methyl.122.9-Deoxy-9-methylene-2a,2b-dihomo-16,16-dimethyl-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 121. 123. Aprostaglandin analog according to claim 120, wherein at least one of R₃and R₄ is fluoro. 124.9-Deoxy-9-methylene-2a,2b-dihomo-16,16-difluoro-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 123. 125. Aprostaglandin analog according to claim 120, wherein R₃ and R₄ are bothhydrogen. 126.9-Deoxy-9-methylene-2a,2b-dihomo-15-methyl-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 125. 127. Aprostaglandin analog according to claim 119, wherein g is one.
 128. Aprostaglandin analog according to claim 127, wherein at least one of R₃and R₄ is methyl.
 129. A prostaglandin analog according to claim 128,wherein R₃ and R₄ are both methyl. 130.9-Deoxy-9-methylene-16,16-dimethyl-13,14-didehydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 129. 131. A prostaglandin analogaccording to claim 127, wherein at least one of R₃ and R₄ is fluoro.132. A prostaglandin analog according to claim 131, wherein R₃ and R₄are both fluoro.
 133. A prostaglandin analog according to claim 132,wherein R₅ is methyl. 134.9-Deoxy-9-methylene-15-methyl-16,16-difluoro-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 133. 135. Aprostaglandin analog according to claim 132, wherein R₅ is hydrogen.136. 9-Deoxy-9-methylene-16,16-difluoro-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 135. 137. Aprostaglandin analog according to claim 127, wherein R₃ and R₄ are bothhydrogen.
 138. A prostaglandin analog according to claim 137, wherein R₅is methyl.
 139. 9-Deoxy-9-methylene-15-methyl-13,14-didehydro-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 138. 140. Aprostaglandin analog according to claim 137, wherein R₅ is hydrogen.141. 9-Deoxy-9-methylene-13,14-didehydro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 140. 142. A prostaglandin analogaccording to claim 1, wherein Y₁ is trans--CH═CH--.
 143. A prostaglandinanalog according to claim 142, wherein Z₇ is cis--CH═CH--CH₂ --(CH₂)_(g)--CF₂ --.
 144. 9-Deoxy-9-methylene-2,2-difluoro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 143. 145. A prostaglandin analogaccording to claim 142, wherein Z₇ is --(CH₂)₃ --(CH₂)_(g) --CF₂ --.146. 9-Deoxy-9-methylene-2,2-difluoro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 145. 147. A prostaglandin analogaccording to claim 142, wherein Z₇ is cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂--.
 148. 9-Deoxy-9-methylene-cis-4,5-didehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 147. 149. A prostaglandin analogaccording to claim 142, wherein Z₇ is --CH₂ --O--CH₂ --(CH₂)_(g) --CH₂--.
 150. 9-Deoxy-9-methylene-5-oxa-PGF₁, 1,15-lactone, a prostaglandinanalog according to claim
 149. 151. A prostaglandin analog according toclaim 142, wherein Z₇ is --C.tbd.C--CH₂ --(CH₂)_(g) --CH₂ --. 152.9-Deoxy-9-methylene-5,6-didehydro-PGF₂, 1,15-lactone, a prostaglandinanalog according to claim
 151. 153. A prostaglandin analog according toclaim 142, wherein Z₇ is --CH₂ --C.tbd.C--(CH₂)_(g) --CH₂ --. 154.9-Deoxy-9-methylene-4,4,5,5-tetradehydro-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 153. 155. A prostaglandin analogaccording to claim 142, wherein Z₇ is --(CH₂)₃ --(CH₂)_(g) --CH₂ --.156. A prostaglandin analog according to claim 155, wherein R₅ is R₅.157. 9-Deoxy-9-methylene-15-epi-PGF₁, 1,15-lactone, a prostaglandinanalog according to claim
 156. 158. A prostaglandin analog according toclaim 155, wherein R₅ is R₅.
 159. A prostaglandin analog according toclaim 158, wherein m is 3, s is zero or one, and T is chloro, fluoro, ortrifluoromethyl.
 160. A prostaglandin analog according to claim 159,wherein g is
 3. 161. 9-Deoxy-9-methylene-2a,2b-dihomo-15-methyl-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 160. 162.9-Deoxy-9-methylene-2a,2b-dihomo-PGF₁, 1,15-lactone, a prostaglandinanalog according to claim
 160. 163. A prostaglandin analog according toclaim 159, wherein g is one.
 164. A prostaglandin analog according toclaim 163, wherein at least one of R₃ and R₄ is methyl.
 165. Aprostaglandin analog according to claim 164, wherein R₃ and R₄ are bothmethyl.
 166. 9-Deoxy-9-methylene-16,16-dimethyl-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 165. 167. A prostaglandin analogaccording to claim 163, wherein at least one of R₃ and R₄ is fluoro.168. A prostaglandin analog according to claim 167, wherein R₃ and R₄are both fluoro.
 169. 9-Deoxy-9-methylene-16,16-difluoro-PGF₁,1,15-lactone, a prostaglandin analog according to claim
 168. 170. Aprostaglandin analog according to claim 163, wherein R₃ and R₄ are bothhydrogen.
 171. A prostaglandin analog according to claim 170, wherein R₅is methyl.
 172. 9-Deoxy-9-methylene-15-methyl-PGF₁, 1,15-lactone, aprostaglandin analog according to claim
 171. 173. A prostaglandin analogaccording to claim 170, wherein R₅ is hydrogen. 174.9-Deoxy-9-methylene-PGF₁, 1,15-lactone, a prostaglandin analog accordingto claim
 173. 175. A prostaglandin analog according to claim 142,wherein Z₇ is cis--CH═CH--CH--CH₂ --(CH₂)_(g) --CH₂ --.
 176. Aprostaglandin analog according to claim 175, wherein R₅ is R₅.
 177. Aprostaglandin analog according to claim 176, wherein m is 3, s is zeroor one, and T is chloro, fluoro, or trifluoromethyl.
 178. Aprostaglandin analog according to claim 177, wherein g is
 3. 179.9-Deoxy-9-methylene-2a,2b-dihomo-15-epi-15-methyl-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 178. 180.9-Deoxy-9-methylene-2a,2b-dihomo-15-epi-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 178. 181. A prostaglandin analogaccording to claim 177, wherein g is one.
 182. A prostaglandin analogaccording to claim 181, wherein at least one of R₃ and R₄ is methyl.183. 9-Deoxy-9-methylene-15-epi-16,16-dimethyl-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 182. 184. A prostaglandin analogaccording to claim 181, wherein at least one of R₃ and R₄ is fluoro.185. 9-Deoxy-9-methylene-15-epi-16,16-difluoro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 184. 186. A prostaglandin analogaccording to claim 181, wherein R₃ and R₄ are both hydrogen. 187.9-Deoxy-9-methylene-15-epi-15-methyl-PGF₂, 1,15-lactone, a prostaglandinanalog according to claim
 186. 188. A prostaglandin analog according toclaim 175, wherein R₅ is R₅.
 189. A prostaglandin analog according toclaim 188, wherein m is 3, s is zero or one, and T is chloro, fluoro, ortrifluoromethyl.
 190. A prostaglandin analog according to claim 189,wherein g is
 3. 191. A prostaglandin analog according to claim 190,wherein at least one of R₃ and R₄ is methyl. 192.9-Deoxy-9-methylene-2a,2b-dihomo-16,16-dimethyl-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 191. 193. A prostaglandin analogaccording to claim 190, wherein at least one of R₃ and R₄ is fluoro.194. 9-Deoxy-9-methylene-2a,2b-dihomo-16,16-difluoro-PGF₂, 1,15-lactone,a prostaglandin analog according to claim
 193. 195. A prostaglandinanalog according to claim 190, wherein R₃ and R₄ are both hydrogen. 196.9-Deoxy-9-methylene-2a,2b-dihomo-15-methyl-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 195. 197. A prostaglandin analogaccording to claim 189, wherein g is one.
 198. A prostaglandin analogaccording to claim 197, wherein at least one of R₃ and R₄ is methyl.199. A prostaglandin analog according to claim 198, wherein R₃ and R₄are both methyl.
 200. 9-Deoxy-9-methylene-16,16-dimethyl-PGF₂,1,15-lactone, a prostaglandin analog according to claim
 199. 201. Aprostaglandin analog according to claim 197, wherein at least one of R₃and R₄ is fluoro.
 202. A prostaglandin analog according to claim 201,wherein R₃ and R₄ are both fluoro.
 203. A prostaglandin analog accordingto claim 202, wherein R₅ is methyl. 204.9-Deoxy-9-methylene-15-methyl-16,16-difluoro-PGF₂, 1,15-lactone, aprostaglandin analog according to claim
 203. 205. A prostaglandin analogaccording to claim 202, wherein R₅ is hydrogen. 206.9-Deoxy-9-methylene-16,16-difluoro-PGF₂, 1,15-lactone, a prostaglandinanalog according to claim
 205. 207. A prostaglandin analog according toclaim 197, wherein R₃ and R₄ are both hydrogen.
 208. A prostaglandinanalog according to claim 207, wherein R₅ is methyl. 209.9-Deoxy-9-methylene-15-methyl-PGF₂, 1,15-lactone, a prostaglandin analogaccording to claim
 208. 210. A prostaglandin analog according to claim207, wherein R₅ is hydrogen.
 211. 9-Deoxy-9-methylene-PGF₂,1,15-lactone, a prostaglandin analog according to claim 210.